Plantings rarely do exactly what you expect, and as the years from their inception stack-up, it becomes increasingly scary and sometimes depressing to continue to visit them, as the combination of ecological process and management (or the lack of) potentially conspire against you. But if we are to be as successful as possible in using planting in cities this is exactly what we must do. We need to steel ourselves, and step outside of the glossy magazine “in the moment” photo mentality and bring a critical, analytical approach to the management of aging vegetation and its initial design-implementation and also the approaches by which we conceptualised and undertook maintenance. James Hitchmough will try to be as honest as possible in doing just this(!) on some of his best (and worst) projects.